CN104507978A - Colored photosensitive composition - Google Patents

Colored photosensitive composition Download PDF

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Publication number
CN104507978A
CN104507978A CN201380040567.5A CN201380040567A CN104507978A CN 104507978 A CN104507978 A CN 104507978A CN 201380040567 A CN201380040567 A CN 201380040567A CN 104507978 A CN104507978 A CN 104507978A
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methyl
halogen atom
compound
acid
substituted
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CN104507978B (en
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久保田裕介
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Adeka Corp
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Asahi Denka Kogyo KK
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/06—Hydroxy derivatives of triarylmethanes in which at least one OH group is bound to an aryl nucleus and their ethers or esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Architecture (AREA)
  • Structural Engineering (AREA)
  • Materials For Photolithography (AREA)
  • Optical Filters (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

The present invention provides a colored photosensitive composition (colored alkali-developable photosensitive composition) having excellent heat resistance and an optical filter using said colored photosensitive composition (colored alkali-developable photosensitive composition), and in particular a color filter which is suitable for image display devices, such as liquid crystal display panels, and does not lower luminance. Specifically, the present invention provides: a colored photosensitive composition containing (A) a dye comprising a compound represented by general formula (I), (B) a polymerizable compound having an ethylenically unsaturated bond, and (C) a photopolymerization initiator; and a color filter for a display device using the colored photosensitive composition. The specific content of general formula (I) is as defined in the description of the present application.

Description

Coloring photosensitive combination
Technical field
The present invention relates to employ be designed to required tone and improve the dyestuff of solvent resistance and thermotolerance, the coloring photosensitive combination of available energy ray polymerization and employ the colour filter of this coloring photosensitive combination.
Background technology
To specific light, there is the optical element that compound that high strength absorbs is used as the image display devices such as the recording layer of the optical record mediums such as CD-R, DVD-R, DVD+R, BD-R or liquid crystal indicator (LCD), plasma display (PDP), electroluminescent display (ELD), CRT display (CRT), fluorescent display tube, field emission display.
In the optical filter of the device used for image display such as liquid crystal indicator (LCD), plasma display (PDP), electroluminescent display (ELD), CRT display (CRT), fluorescent display tube, field emission display, the various compounds absorbing the light of 300 ~ 1100nm wavelength are used as light absorber.
For these light absorbers, require photoabsorption peak width at half height that is precipitous especially, i.e. λ max little and can not because of losses of function such as light and heats.
Colour filter is had in the optical filter being mainly used in liquid crystal indicator (LCD).Although general 3 primary colors using RGB, use independent coloured material to be difficult to hold the tone of pure RGB, make great efforts to use multiple coloured material with the tone close to pure RGB in colour filter all the time.Therefore, the coloured materials such as the yellow of non-RGB, orange, purple are also needed.
For in the light absorber of colour filter, use organic and/or mineral dye according to the height of thermotolerance, but there is the problem that the brightness as display unit can be made to reduce owing to being pigment, solve this problem by the brightness improving light source.But along with the trend of power reducing, the exploitation employing the colour filter of dyestuff is prevailing.
And then, in recent years, in the colour filter of solid-state imager, improving from the view point of picture quality, require the filming of colored pattern, in order to carry out filming, needing from the aspect of depth of shade to improve dye strength.In addition, when the molar absorbance backscatter extinction logarithmic ratio of dyestuff is low, need to add a large amount of dyestuffs.
But, following problem can be there is when improving dye strength: visible pigment stripping or precipitation from formation pixel after film forming; Or easily there is colour mixture between levels when implementing heat treated (curing afterwards) after film forming between neighbor or in stepped construction.
The colour filter colored resin composition of the triarylmethane system pigment containing ad hoc structure is disclosed in patent documentation 1 and 2.
But the triarylmethane system pigment recorded in these documents is failed satisfactory in thermotolerance.
Prior art document
Patent documentation
Patent documentation 1: Japanese Unexamined Patent Publication 2010-204132 publication
Patent documentation 2: Japanese Unexamined Patent Publication 2012-017425 publication
Summary of the invention
The technical problem that invention will solve
Therefore, the object of the present invention is to provide the coloring photosensitive combination of excellent heat resistance (painted alkali-developable photosensitive composition).In addition, the optical filter employing above-mentioned coloring photosensitive combination (painted alkali-developable photosensitive composition), the colour filter being suitable for the image display devices such as display panels that particularly brightness can not be made to reduce are provided provide.
For the method for technical solution problem
Present inventor has performed further investigation repeatedly, found that: the excellent heat resistance with the compound of ad hoc structure, excellent solvent resistance with regard to coloring photosensitive combination (painted alkali-developable photosensitive composition), find in addition: above-mentioned coloring photosensitive combination (painted alkali-developable photosensitive composition) can not make the brightness of optical filter (particularly colour filter) reduce, be suitable for the device used for image display colour filters such as display panels, thus complete the present invention.
The present invention makes in view of above-mentioned discovery, its object is to the coloring photosensitive combination providing a kind of dyestuff (A), the polymerizable compound (B) with ethylenic unsaturated link(age) and Photoepolymerizationinitiater initiater (C) containing being made up of the compound shown in following general formula (I).
(in formula, R 1, R 2, R 3, R 20, R 21, R 22, R 23, R 24, R 25, R 26, R 27and R 28represent hydrogen atom or halogen atom independently of one another, be the alkyl of 1 ~ 8 by cyano group, nitro, hydroxyl, the substituted or unsubstituted carbonatoms of halogen atom, by the substituted or unsubstituted carbonatoms of halogen atom be 6 ~ 12 aryl, be the arylalkyl of 7 ~ 20 or the substituting group that represents with-X-Y by the substituted or unsubstituted carbonatoms of halogen atom; X represents Sauerstoffatom or sulphur atom; Y represent by the substituted or unsubstituted carbonatoms of halogen atom be 1 ~ 8 alkyl, be the aryl of 6 ~ 12 by the substituted or unsubstituted carbonatoms of halogen atom or be the arylalkyl of 7 ~ 20 by the substituted or unsubstituted carbonatoms of halogen atom;
R 4, R 5, R 6, R 7, R 8and R 9represent hydroxyl or halogen atom independently of one another, be the alkyl of 1 ~ 8 by the substituted or unsubstituted carbonatoms of cyano group, nitro, hydroxyl or halogen atom, by carbonatoms be 1 ~ 4 alkyl, halogen atom, cyano group or vinyl substituted or unsubstituted phenyl, by carbonatoms be 1 ~ 4 alkyl, halogen atom, cyano group or vinyl substituted or unsubstituted benzyl; R 4with R 5, R 6with R 7, and R 8with R 9also can be connected to form the heterocycle of 3 ~ 6 rings;
R 1, R 2and R 3in at least 2 be substituting group beyond hydrogen atom;
An q-represent the negatively charged ion of q valency, q represent 1 or 2, p represent electric charge remained neutral coefficient.)
In addition, the present invention provide a kind of use to have alkali-developable as the optimal way of above-mentioned coloring photosensitive combination the polymerizable compound (B') with ethylenic unsaturated link(age) as the above-mentioned coloring photosensitive combination (painted alkali-developable photosensitive composition) with alkali-developable with the polymerizable compound (B) of ethylenic unsaturated link(age).
In addition, the invention provides the cured article of above-mentioned coloring photosensitive combination (painted alkali-developable photosensitive composition) and use the display device colour filter of this cured article.
Invention effect
Containing the excellent heat resistance of coloring photosensitive combination of the present invention (painted alkali-developable photosensitive composition) of compound with ad hoc structure.And its cured article is suitable for display device colour filter.
Embodiment
Below, based on preferred implementation, the present invention will be described.
First, coloring photosensitive combination of the present invention is described.In the following description, suitably coloring photosensitive combination or painted alkali-developable composition described later are recited as coloured composition.
Coloured composition of the present invention contains the dyestuff (A) (below also referred to as dyestuff (A)) be made up of the compound shown in above-mentioned general formula (I), there is polymerizable compound (B) (comprising having gives the alkali-soluble of alkali-developable the substituent polymerizable compound (B ') with ethylenic unsaturated link(age)) and the Photoepolymerizationinitiater initiater (C) of ethylenic unsaturated link(age), and more than one the coloured material contained as required (but except the dyestuff be made up of the compound shown in above-mentioned general formula (I)) (D).Below each composition is described in order.
< dyestuff (A) >
The dyestuff (A) used in the present invention is as long as containing the compound shown at least a kind of above-mentioned general formula (I), can be used alone or combine multiple use.In addition, dyestuff (A), except the compound shown in above-mentioned general formula (I), can also use known dyestuff.As known dyestuff, such as can enumerate the dyestuffs etc. such as azoic dyestuff, anthraquinone dye, indigoide colors, triarylmethane dye, xanthene dye, alizarine dyestuff, acridine dye, Stilbene dyestuff, thiazole dye, naphthol dye, quinoline dye, nitro-dye, phenylene blue dyestuff, oxazine dye, phthalocyanine pigment, cyanine dyes, they can mix multiple use.
As the R in above-mentioned general formula (I) 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8and R 9and R 1, R 2and R 3unsubstituted carbonatoms when being represented by-X-Y represented by Y is the alkyl of 1 ~ 8, can enumerate methyl, ethyl, propyl group, sec.-propyl, butyl, sec-butyl, the tertiary butyl, isobutyl-, amyl group, isopentyl, tert-pentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 1-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, different heptyl, tertiary heptyl, 1-octyl group, iso-octyl, tertiary octyl group etc.;
As R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8and R 9the shown carbonatoms replaced by halogen atom, cyano group, nitro, hydroxyl is the alkyl of 1 ~ 8, can enumerate part or all group replaced by halogen atom, cyano group, nitro, hydroxyl that above-mentioned carbonatoms is the hydrogen atom in the alkyl of 1 ~ 8;
As R 1, R 2and R 3and R 1, R 2and R 3unsubstituted carbonatoms when being represented by-X-Y represented by Y is the aryl of 6 ~ 12, phenyl can be enumerated, naphthyl, 2-aminomethyl phenyl, 3-aminomethyl phenyl, 4-aminomethyl phenyl, 4-ethenylphenyl, 3-isopropyl phenyl, 4-isopropyl phenyl, 4-butyl phenyl, 4-isobutyl phenenyl, 4-tert-butyl-phenyl, 4-hexyl phenyl, 4-cyclohexyl phenyl, 2, 3-3,5-dimethylphenyl, 2, 4-3,5-dimethylphenyl, 2, 5-3,5-dimethylphenyl, 2, 6-3,5-dimethylphenyl, 3, 4-3,5-dimethylphenyl, 3, 5-3,5-dimethylphenyl, (1, 1 '-biphenyl)-4-base, 2, 4, 5-trimethylphenyl, ferrocenyl etc.,
As R 1, R 2and R 3and R 1, R 2and R 3unsubstituted carbonatoms when being represented by-X-Y represented by Y is the arylalkyl of 7 ~ 20, can enumerate benzyl, styroyl, 2-phenyl-propane-2-base, diphenyl methyl, trityl group, styryl, cinnamyl, ferrocenyl methyl, ferrocenyl propyl group etc.
As by the R in above-mentioned general formula (I) 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8and R 9shown carbonatoms is alkyl and the R of 1 ~ 8 4, R 5, R 6, R 7, R 8and R 9the halogen atom that shown phenyl or benzyl replace, can enumerate fluorine, chlorine, bromine, iodine;
As by R 4, R 5, R 6, R 7, R 8and R 9the carbonatoms that shown phenyl or benzyl replace is the alkyl of 1 ~ 4, can enumerate methyl, ethyl, propyl group, sec.-propyl, butyl, sec-butyl, the tertiary butyl, isobutyl-etc.
In above-mentioned general formula (I), as R 4with R 5, R 6with R 7, and R 8with R 9the heterocycle of 3 ~ 6 rings that can be connected to form, piperidine ring, piperazine ring, pyrrolidine ring, morpholine ring, thiomorpholine ring, pyridine ring, pyrazine ring, pyrimidine ring, quinoline ring, isoquinoline 99.9 ring, imidazole ring, oxazole ring, imidazolidine ring, pyrazolidine ring, isoxazole alkyl ring, isothiazolidine ring etc. can be enumerated, these rings can with other cyclic condensations, also can be substituted.
In compound shown in above-mentioned general formula (I), R 1, R 2and R 3in at least 2 be substituting group beyond hydrogen atom.
As the An in above-mentioned general formula (I) q-shown negatively charged ion, such as, as monovalent ion, can enumerate the halide ionss such as chloride ion, bromide ion, iodide ion, fluoride ion, the inorganic series anions such as high chloro acid ion, chlorate ions, thiocyanate ion, hexafluorophosphate ion, hexafluoro-antimonic acid ion, Tetrafluoroboric acid ion, methanesulfonic ion, dodecyl sodium sulfonate ion, Phenylsulfonic acid ion, toluenesulphonic acids ion, trifluoromethayl sulfonic acid ion, naphthene sulfonic acid ion, diphenylamine-4-azochlorosulfonate acid ion, 2-amino-4-methyl-5-chloro Phenylsulfonic acid ion, 2-amino-5-nitrobenzene-sulfonic acid ion, Japanese Unexamined Patent Publication 10-235999, Japanese Unexamined Patent Publication 10-337959, Japanese Unexamined Patent Publication 11-102088, Japanese Unexamined Patent Publication 2000-108510, Japanese Unexamined Patent Publication 2000-168223, Japanese Unexamined Patent Publication 2001-209969, Japanese Unexamined Patent Publication 2001-322354, Japanese Unexamined Patent Publication 2006-248180, Japanese Unexamined Patent Publication 2006-297907, Japanese Unexamined Patent Publication 8-253705 publication, Japanese Unexamined Patent Application Publication 2004-503379 publication, Japanese Unexamined Patent Publication 2005-336150 publication, the organic sulfonic acid series anions such as azochlorosulfonate acid ion described in International Publication No. 2006/28006 publication etc., octylphosphonic acid ion, dodecylphosphoric acid ion, octadecyl phosphate ion, phosphenylic acid ion, nonyl phenyl phosphate ion, 2, the organic phosphoric acid series anions such as 2 '-methylene-bis (4,6-di-tert-butyl-phenyl) phosphonic acids ion, two fluoroform sulfimide ion, two perfluorinated butane sulfimide ion, perfluor-4-ethylcyclohexane azochlorosulfonate acid ion, four (pentafluorophenyl group) borate ion, three (oroalkane sulfonyl base) carbanion etc., as divalent ion, such as, can enumerate benzene disulfonic acid ion, naphthalene disulfonic acid ion etc.In addition, the quencher negatively charged ion with bioactive molecule de-excitation (making its cancellation) function making to be in excited state or the Metallocenic compound such as ferrocene, the ruthenocene negatively charged ion etc. in cyclopentadienyl rings with carboxyl or the anionic property such as phosphonate group, sulfonic group group can also be used as required.In addition, the mode that p reaches neutrality according to the electric charge of molecular entities is selected.
As above-mentioned quencher negatively charged ion, such as can enumerate Japanese Laid-Open Patent Publication 60-234892 publication, Japanese Unexamined Patent Publication 5-43814 publication, Japanese Unexamined Patent Publication 5-305770 publication, Japanese Unexamined Patent Publication 6-239028 publication, Japanese Unexamined Patent Publication 9-309886 publication, Japanese Unexamined Patent Publication 9-323478 publication, Japanese Unexamined Patent Publication 10-45767 publication, Japanese Unexamined Patent Publication 11-208118 publication, Japanese Unexamined Patent Publication 2000-168237 publication, Japanese Unexamined Patent Publication 2002-201373 publication, Japanese Unexamined Patent Publication 2002-206061 publication, Japanese Unexamined Patent Publication 2005-297407 publication, Japanese Patent Publication 7-96334 publication, the negatively charged ion recorded in International Publication No. 98/29257 publication etc.
As the An in above-mentioned general formula (I) q-shown negatively charged ion, from the aspect of thermotolerance, the organic sulfonic acid series anion of preferred monovalence, two fluoroform sulfimide ion, two perfluorinated butane sulfimide ion, perfluor-4-ethylcyclohexane azochlorosulfonate acid ion, benzene disulfonic acid ion, naphthalene disulfonic acid ion, more preferably two fluoroform sulfimide ion.
As the object lesson of the cationic moiety of the compound shown in above-mentioned general formula (I) of the present invention, can enumerate following compound N o.1 ~ No.29.
In compound shown in above-mentioned general formula (I), preferred following compound.
R 1, R 2and R 3from the preferred halogen atom in the aspect of thermotolerance, be the alkyl of 1 ~ 8 or the substituting group that represents with-X-Y by the substituted or unsubstituted carbonatoms of halogen atom, particularly preferably R 1, R 2and R 3in any more than 2 be halogen atom, be the alkyl of 1 ~ 8 by the substituted or unsubstituted carbonatoms of halogen atom.
R 4, R 5, R 6, R 7, R 8and R 9preferably to be optionally substituted by a hydroxyl group from the aspect of solvent solubility or unsubstituted carbonatoms is the alkyl of 1 ~ 8.
The manufacture method of the compound shown in above-mentioned general formula (I) is not particularly limited, such as, can manufacture according to following reaction formula.
(in formula, R 1~ R 9identical with above-mentioned general formula (I).)
In dyestuff used in the present invention (A), the compound shown in above-mentioned general formula (I) can use a kind or used in combination multiple, and its total content is preferably 50 ~ 100 quality %, is more preferably 70 ~ 100 quality %.When the content of the compound shown in above-mentioned general formula (I) of the present invention is less than 50 quality %, solvability in a solvent reduces or thermotolerance reduces sometimes.
In coloured composition of the present invention, the content of above-mentioned dyestuff (A) is preferably 0.01 ~ 50 quality %, is more preferably 0.1 ~ 30 quality % in coloured composition of the present invention.When the content of dyestuff (A) is less than 0.01 quality %, the cured article of coloured composition of the present invention cannot obtain the color of desired concn sometimes, and when being greater than 50 quality %, dyestuff (A) occurring sometimes and separates out in coloured composition.
< has polymerizable compound (B) > of ethylenic unsaturated link(age)
Be not particularly limited as the above-mentioned polymerizable compound (B) with ethylenic unsaturated link(age), the polymerizable compound in the past used in photosensitive composite can be used, such as, can enumerate the unsaturated fatty hydrocarbons such as ethene, propylene, butylene, iso-butylene, vinylchlorid, vinylidene chloride, vinylidene, tetrafluoroethylene, (methyl) vinylformic acid, α-chloroacrylic acid, methylene-succinic acid, toxilic acid, citraconic acid, fumaric acid, nadic acid, β-crotonic acid, iso-crotonic acid, vinylacetic acid, allyl acetic acid, styracin, Sorbic Acid, methylfumaric acid, mono succinate [2-(methyl) acryloyl-oxyethyl] ester, phthalic acid list [2-(methyl) acryloyl-oxyethyl] ester, ω-carboxy-polycaprolactone list (methyl) acrylate etc. have list (methyl) acrylate of the polymkeric substance of carboxyl and hydroxyl at two ends, hydroxyethyl (methyl) acrylate maleic acid ester, hydroxypropyl (methyl) acrylate maleic acid ester, the unsaturated polyprotonic acid such as Dicyclopentadiene (DCPD) maleic acid ester or multifunctional (methyl) acrylate with 1 carboxyl and more than 2 (methyl) acryls, (methyl) 2-Hydroxy ethyl acrylate, (methyl) 2-hydroxypropyl acrylate, (methyl) glycidyl acrylate, following compound N o.A1 ~ No.A4, (methyl) methyl acrylate, (methyl) butyl acrylate, (methyl) isobutyl acrylate, (methyl) tert-butyl acrylate, (methyl) cyclohexyl acrylate, (methyl) n-octyl, (methyl) Isooctyl acrylate monomer, (methyl) vinylformic acid ester in the different ninth of the ten Heavenly Stems, (methyl) stearyl acrylate ester, (methyl) lauryl acrylate, (methyl) methoxyethyl acrylate, (methyl) acrylate methyl esters, (methyl) dimethylaminoethyl acrylate, (methyl) acrylic-amino propyl ester, (methyl) acrylate propyl ester, (methyl) ethoxyethyl acrylate, (methyl) vinylformic acid gathers (oxyethyl group) ethyl ester, (methyl) acrylate, butoxy ethoxy ethyl ester, (methyl) EHA, (methyl) acrylate, (methyl) vinylformic acid tetrahydrofuran ester, (methyl) vinyl acrylate, (methyl) allyl acrylate, (methyl) benzyl acrylate, ethylene glycol bisthioglycolate (methyl) acrylate, Diethylene Glycol two (methyl) acrylate, triethylene glycol two (methyl) acrylate, polyoxyethylene glycol two (methyl) acrylate, propylene glycol two (methyl) acrylate, BDO two (methyl) acrylate, 1,6-hexylene glycol two (methyl) acrylate, trimethylolethane trimethacrylate (methyl) acrylate, trimethylolpropane tris (methyl) acrylate, Dipentaerythritol five (methyl) acrylate, Dipentaerythritol six (methyl) acrylate, tetramethylolmethane four (methyl) acrylate, tetramethylolmethane three (methyl) acrylate, tristane dihydroxymethyl two (methyl) acrylate, three [(methyl) acryloyl ethyl] isocyanuric acid ester, the ester of the unsaturated monoprotic acid such as polyester (methyl) origoester acrylate and polyvalent alcohol or polyphenol, the metal-salt of the unsaturated polyprotonic acids such as (methyl) zinc acrylate resin, (methyl) Magnesium Acrylate Prepared, maleic anhydride, itaconic anhydride, citraconic anhydride, methyl tetrahydrophthalic anhydride, Tetra Hydro Phthalic Anhydride, trialkyl Tetra Hydro Phthalic Anhydride, 5-(2,5-dioxotetrahydrofuryl) acid anhydrides of the unsaturated polyprotonic acid such as-3-methyl-3-tetrahydrobenzene-1,2-dicarboxylic anhydride, trialkyl Tetra Hydro Phthalic Anhydride-maleic anhydride adduct, dodecenylsuccinic anhydride, methyl norbornene dioic anhydride, the acid amides of the unsaturated monoprotic acid such as (methyl) acrylamide, methylene-bis (methyl) acrylamide, diethylenetriamine three (methyl) acrylamide, xylylene two (methyl) acrylamide, α-chloroacrylamide, N-2-hydroxyethyl (methyl) acrylamides and polyamine, the unsaturated aldehydes such as propenal, the unsaturated nitriles such as (methyl) vinyl cyanide, α-chloro-acrylonitrile, vinylidene dicyanide, allyl cyanide, the unsaturated aromatics such as vinylbenzene, 4-vinyl toluene, 4-ethyl styrene, 4-methoxy styrene, 4-Vinyl phenol, 4-chloro-styrene, Vinylstyrene, Vinyl toluene, vinyl benzoic acid, vinylphenol, vinyl sulfonic acid, 4-vinylbenzenesulfonic acid, vinyl benzyl methyl ether, vinylbenzyl glycidyl ether, the beta-unsaturated ketones such as methyl vinyl ketone, the unsaturated amine compounds such as vinyl amine, allyl amine, NVP, vinylpiperidine, the vinyl alcohol such as vinyl carbinol, crotyl alcohol, the vinyl ether such as vinyl methyl ether, EVE, n-butyl vinyl ether, IVE, glycidyl allyl ether, the unsaturated acid imides such as maleimide, N-phenylmaleimide, N-N-cyclohexylmaleimide, the indenes classes such as indenes, 1-methyl indenes, the aliphatic conjugated diene classes such as 1,3-butadiene, isoprene, chloroprene, polystyrene, poly-(methyl) methyl acrylate, poly-(methyl) n-butyl acrylate, polysiloxane etc. have the macromonomer class of list (methyl) acryl at the end of polymer molecular chain, vinyl chloride, vinylidene chloride, divinyl succinate ester, Phthalic acid, diallyl ester, triallyl phosphate, triallyl isocyanurate, vinyl sulfide, vinyl imidazole, Yi Xi oxazolin, vinylcarbazole, vinyl pyrrolidone, vinyl pyridine, the vinyl carbamate compound of the vinyl monomer containing hydroxyl and polyisocyanate compounds, vinyl monomer containing hydroxyl and the vinyloxirane of polyepoxides, pentaerythritol triacrylate, Dipentaerythritol Pentaacrylate etc. contain polyfunctional acrylic ester and the tolylene diisocyanate of hydroxyl, the reactant of the polyfunctional isocyanates such as hexamethylene diisocyanate, as pentaerythritol triacrylate, Dipentaerythritol Pentaacrylate etc. contain polyfunctional acrylic ester and the succinyl oxide of hydroxyl, Tetra hydro Phthalic anhydride, the reactant of the dibasic acid anhydrides such as Tetra Hydro Phthalic Anhydride and there is the polyfunctional acrylic ester of acid number.
These polymerizable compounds can be used alone or are mixed with two or more, and when being mixed with two or more, use after they copolymerization in advance can being made multipolymer.
In addition, in coloured composition of the present invention, as the above-mentioned polymerizable compound (B) with ethylenic unsaturated link(age), when use have the alkali-soluble can giving alkali-developable substituent there is ethylenic unsaturated link(age) polymerizable compound (B ') (the alkali-developable compound (B ') hereinafter also referred to having ethylenic unsaturated link(age)) time, coloring photosensitive combination of the present invention becomes painted alkali-developable photosensitive composition.As this, there is the alkali-developable compound (B ') of ethylenic unsaturated link(age), (methyl) vinylformic acid can be used, (methyl) methyl acrylate, (methyl) ethyl propenoate, (methyl) propyl acrylate, (methyl) isopropyl acrylate, (methyl) butyl acrylate, (methyl) isobutyl acrylate, (methyl) tert-butyl acrylate, (methyl) benzyl acrylate, (methyl) phenyl acrylate, (methyl) cyclohexyl acrylate, (methyl) acrylate, (methyl) 2-EHA, (methyl) isobornyl acrylate, (methyl) vinylformic acid 2-hydroxy methacrylate, (methyl) esters of acrylic acids such as (methyl) tetrahydrofurfuryl acrylate, NVP, the styrenic such as Styrene and its derivatives, alpha-methyl styrene, the acrylic amides such as (methyl) acrylamide, methylol (methyl) acrylamide, alkoxyl group methylol (methyl) acrylamide, diacetone (methyl) acrylamide, (methyl) vinyl cyanide, ethene, propylene, butylene, vinylchlorid, other vinyl compound such as vinyl-acetic ester, and polymethylmethacrylate macromonomer, the macromonomer classes such as Group-capped Polystyrene Macromer, the monomethacrylates of tricyclodecane skeleton, N-phenylmaleimide, the multipolymers acrylic acid with (methyl) such as methacryloxymethyl-3-Ethyloxetane, and make they and Inc. of Showa Denko K. K KARENZ MOI, the isocyanate compound of what AOI was such have unsaturated link(age) reacts and obtains (methyl) acrylic acid multipolymer, make phenol and/or cresol novolac epoxy, there is biphenyl backbone, the epoxy group(ing) of epoxy compounds that the novolak type epoxy compounds such as phenolic resin varnish, bisphenol A novolac type epoxy compounds, dicyclopentadiene novolac type epoxy compounds of naphthalene skeleton, the polyphenylene methane type epoxy resin with multi-functional epoxy's base, following general formula (1) represent etc. and unsaturated monoprotic acid effect the resin making itself and multi-anhydride effect further and obtain.These monomers can be used alone a kind or two or more is used in combination.In addition, the above-mentioned unsaturated group of alkali-developable compound (B ') preferably containing 0.2 ~ 1.0 equivalent with ethylenic unsaturated link(age).
(in formula, X 1the ester ring type alkyl that the alkylidene that expression Direct Bonding, methylene radical, carbonatoms are 1 ~ 4, carbonatoms are 3 ~ 20 ,-O-,-S-,-SO 2-,-SS-,-SO-,-CO-,-OCO-or following formula (i), (ii) or the substituting group shown in (iii), this alkylidene can also be replaced by halogen atom, R 16, R 17, R 18and R 19represent that hydrogen atom, carbonatoms are alkyl, the carbonatoms alkoxyl group that is 1 ~ 8, carbonatoms be 2 ~ 5 alkenyl or the halogen atom of 1 ~ 5 independently of one another, abovementioned alkyl, alkoxyl group and alkenyl can also be replaced by halogen atom, and r is the integer of 0 ~ 10.)
(in formula, Z 1expression can by carbonatoms be 1 ~ 10 alkyl or carbonatoms be 1 ~ 10 alkoxyl group replace phenyl, can by carbonatoms be 1 ~ 10 alkyl or carbonatoms be 1 ~ 10 alkoxyl group replace carbonatoms be 3 ~ 10 cycloalkyl or hydrogen atom, Y 1represent that carbonatoms is alkyl, the carbonatoms alkoxyl group that is 1 ~ 10, carbonatoms be 2 ~ 10 alkenyl or halogen atom, the above-mentioned Y of 1 ~ 10 1in alkyl, alkoxyl group and alkenyl can also be replaced by halogen atom, b is the integer of 0 ~ 5.)
(in formula, Y 2and Z 2represent the carbonatoms that can be replaced by halogen atom is the alkyl of 1 ~ 10, the carbonatoms that can be replaced by halogen atom is 6 ~ 20 aryl independently of one another, aromatic yl alkenyl that aryloxy that the carbonatoms that can be replaced by halogen atom is 6 ~ 20, artyl sulfo that the carbonatoms that can be replaced by halogen atom is 6 ~ 20, the carbonatoms that can be replaced by halogen atom are 8 ~ 20, arylalkyl that the carbonatoms that can be replaced by halogen atom is 7 ~ 20, the carbonatoms that can be replaced by halogen atom be 2 ~ 20 heterocyclic radical, combination have group or the halogen atom of these groups multiple, above-mentioned Y 2and Z 2in alkyl and methylene radical in arylalkyl also can be interrupted by unsaturated link(age) ,-O-or-S-, Z 2also can at adjacent Z 12between form ring, p represents the integer of 0 ~ 4, and q represents the integer of 0 ~ 8, and r represents the integer of 0 ~ 4, and s represents the integer of 0 ~ 4, and the numerical value sum of r and s is the integer of 2 ~ 4.)
As the above-mentioned unsaturated monoprotic acid of the epoxy group(ing) effect with above-mentioned epoxy compounds, vinylformic acid, methacrylic acid, β-crotonic acid, styracin, Sorbic Acid, hydroxyethyl meth acrylate maleic acid ester etc. can be enumerated.Hydroxy ethyl methacrylate maleic acid ester, HPMA maleic acid ester, hydroxypropyl acrylate maleic acid ester, Dicyclopentadiene (DCPD) maleic acid ester etc. can be enumerated.
In addition, as the above-mentioned multi-anhydride of having an effect after making above-mentioned unsaturated monoprotic acid effect, bibenzene tetracarboxylic dianhydride can be enumerated, Tetra Hydro Phthalic Anhydride, succinyl oxide, maleic anhydride, trimellitic acid 1,2-anhydride, pyromellitic dianhydride, 2, 2 '-3, 3 '-benzophenone tetracarboxylic anhydride, two trimellitic acid 1,2-anhydride glycol ester, three trimellitic acid 1,2-anhydride glyceryl ester, hexahydrophthalic anhydride, methyl tetrahydrophthalic anhydride, carbic anhydride, methylnadic anhydride, trialkyl Tetra Hydro Phthalic Anhydride, hexahydrophthalic anhydride, 5-(2, 5-dioxotetrahydrofuryl)-3-methyl-3-tetrahydrobenzene-1, 2-dicarboxylic anhydride, trialkyl Tetra Hydro Phthalic Anhydride-maleic anhydride adduct, dodecenylsuccinic anhydride, methyl norbornene dioic anhydride etc.
Described in the reaction mol ratio of above-mentioned epoxy compounds, above-mentioned unsaturated monoprotic acid and above-mentioned multi-anhydride is preferably as follows.That is: have relative to above-mentioned epoxy compounds 1 epoxy group(ing), carry out in the epoxy adduct of the structure that addition obtains with 0.1 ~ 1.0 above-mentioned unsaturated monacid carboxyl, preferably reaching relative to the acid anhydride structure of 1 hydroxyl of this epoxy adduct, above-mentioned multi-anhydride is the ratio of 0.1 ~ 1.0.
The reaction of above-mentioned epoxy compounds, above-mentioned unsaturated monoprotic acid and above-mentioned multi-anhydride can conventionally be carried out.
In order to the developability by regulating acid number to improve the coloured composition of the present invention as painted alkali-developable photosensitive composition, simple function or multi-functional epoxy compound can be used further together with the above-mentioned alkali-developable compound with ethylenic unsaturated link(age).The above-mentioned acid number with the preferred solids component of alkali-developable compound of ethylenic unsaturated link(age) is the scope of 5 ~ 120mgKOH/g, and the usage quantity of simple function or multi-functional epoxy compound is preferably selected in the mode meeting above-mentioned acid number.
As above-mentioned monofunctional epoxy compound, glycidyl methacrylate can be enumerated, methyl glycidyl ether, ethyl ether, propyl glycidyl ether, isopropyl glycidyl ether, butylglycidyl ether, isobutyl glycidyl ether, tertiary butyl glycidyl ether, amyl group glycidyl ether, hexyl glycidyl ether, heptyl glycidyl ether, octyl glycidyl ether, nonyl glycidyl ether, decyl glycidyl ether, undecyl glycidyl ether, lauryl diglycidyl ether, tridecyl glycidyl ether, tetradecyl glycidyl ether, pentadecyl glycidyl ether, cetyl glycidyl ether, 2-hexyl glycidyl ether, glycidyl allyl ether, propargyl glycidyl ether, to methoxy ethyl glycidyl ether, phenyl glycidyl ether, to methoxyl group glycidyl ether, p-butylphenol glycidyl ether, cresylglycidylether, 2-methacresol glycidyl ether, 4-nonyl phenyl glycidyl glyceryl ether, benzyl glycidyl ether, to cumyl phenyl glycidyl ether, trityl glycidyl ether, 2,3-epoxypropyl methacrylic ester, epoxidised soybean oil, epoxidation linseed oil, Glycidyl butyrate, single ethylene oxide butylcyclohexane, 1,2-epoxy-4-vinyl cyclohexane, Styrene oxide 98min., pinene oxide, oxidation methyl vinylbenzene, cyclohexene oxide, propylene oxide, above-claimed cpd No.A2, No.A3 etc.
As above-mentioned multi-functional epoxy compound, when use be selected from biphenol type epoxy compound and Racemic glycidol ethers more than one time, can the better painted alkali-developable photosensitive composition of acquired character, thus preferably.As this biphenol type epoxy compound, except can using the epoxy compounds shown in above-mentioned general formula (1), such as, can also use the biphenol type epoxy compounds such as A Hydrogenated Bisphenol A type epoxy compounds.As this Racemic glycidol ethers, ethylene glycol diglycidylether can be enumerated, propylene glycol diglycidylether, 1, 4-butanediol diglycidyl ether, 1, 6-hexanediol diglycidyl ether, 1, 8-ethohexadiol diglycidylether, 1, 10-decanediol diglycidylether, 2, 2-dimethyl-1, ammediol diglycidylether, diethylene glycol diglycidyl glyceryl ether, Triethylene Glycol Diglycidyl Ether, TEG diglycidylether, six ethylene glycol diglycidylethers, 1, 4-cyclohexanedimethanodiglycidyl diglycidyl ether, 1, 1, 1-tri-(glycidyl oxy methyl) propane, 1, 1, 1-tri-(glycidyl oxy methyl) ethane, 1, 1, 1-tri-(glycidyl oxy methyl) methane, 1, 1, 1, 1-tetra-(glycidyl oxy methyl) methane.
In addition, the novolak type epoxy compounds such as phenol novolak-type epoxy compound, biphenyl novolak type epoxy compounds, cresol novolak type epoxy compound, bisphenol A novolac type epoxy compounds, dicyclopentadiene novolac type epoxy compounds can also be used; The cycloaliphatic epoxy such as 3,4-epoxy-6-methylcyclohexylmethyl-3,4-epoxy-6-methylcyclohexanecarboxylic acid ester, 3,4-epoxycyclohexyl-methyl-3,4-epoxycyclohexane carboxylate, 1-epoxy ethyl-3,4-epoxy cyclohexane; The glycidyl ester classes such as o-phthalic acid diglycidyl ester, tetrahydrophthalic acid 2-glycidyl ester, dipolymer acid glycidyl ester; The glycidyl amines such as four glycidyl group diaminodiphenyl-methane, triglycidyl group p-aminophenol, N, N-diglycidylaniline; The hetero ring type epoxy compoundss such as 1,3-diglycidyl-5,5-T10, triglycidyl group isocyanuric acid ester; The dioxide compound such as titanium dioxide Dicyclopentadiene (DCPD); Naphthalene type epoxy compounds, triphenylmethane type epoxy compound, dicyclopentadiene type epoxy compound etc.
In the above-mentioned polymerizable compound (B) (comprising the above-mentioned alkali-developable compound (B ') with ethylenic unsaturated link(age)) with ethylenic unsaturated link(age), from the aspect of consistency, alkali-developable and thermotolerance, preferred unsaturated fatty hydrocarbons, unsaturated polyprotonic acid, the polyfunctional acrylic ester with acid number, (methyl) esters of acrylic acid, more preferably unsaturated fatty hydrocarbons and unsaturated polyprotonic acid.
In coloured composition of the present invention, the content of the above-mentioned polymerizable compound (B) (comprising the above-mentioned alkali-developable compound (B ') with ethylenic unsaturated link(age)) with ethylenic unsaturated link(age) is preferably 30 ~ 99 quality %, is particularly preferably 60 ~ 95 quality % in coloured composition of the present invention.When the above-mentioned content with the polymerizable compound (B) of ethylenic unsaturated link(age) is less than 30 quality %, the mechanical strength of cured article is not enough and crack sometimes, or fault occurs when having alkali-developable to develop sometimes; And when more than 99 quality %, sometimes utilize and expose the solidification carried out and become insufficient and become sticky, or when sometimes developing when having alkali-developable, time elongated, cured portion also causes film destroy because of alkali.
< Photoepolymerizationinitiater initiater (C) >
As above-mentioned Photoepolymerizationinitiater initiater (C), in the past known compound can be used, such as, can enumerate benzophenone, phenylbiphenylyl ketone, 1-hydroxyl-1-2-benzoyl-cyclohexane, bitter almond oil camphor, benzyl dimethyl ketal, 1-benzyl-1-dimethylamino-1-(4 '-morpholino benzoyl) propane, 2-morpholinyl-2-(4 '-methyl mercapto) benzoyl propane, thioxanthone, the chloro-4-propoxythioxanthone of 1-, isopropyl thioxanthone, diethyl thioxanthone, EAQ, 4-benzoyl-4 '-dimethyl diphenyl sulfide, benzoin butyl ether, 2-hydroxyl-2-benzoyl propane, 2-hydroxyl-2-(4 '-sec.-propyl) benzoyl propane, 4-butylbenzoyl trichloromethane, 4-phenoxybenzoyl methylene dichloride, methyl benzoylformate, two (9 '-acridyl) heptane of 1,7-, two (the 2 '-morpholino isobutyryl) carbazole of 9-normal-butyl-3,6-, two (trichloromethyl) s-triazine of 2-methyl-4,6-, two (trichloromethyl) s-triazine of 2-phenyl-4,6-, two (trichloromethyl) s-triazine of 2-naphthyl-4,6-, two (the 2-chloro-phenyl-)-4,5 of 2,2-, 4 ', 5 '-tetraphenyl-1-2 '-bisglyoxaline, 4,4-Diisopropyl azodicarboxylate, triphenylphosphine, camphorquinone, benzoyl peroxides etc., as commercially available product, can enumerate N-1414, N-1717, N-1919, PZ-408, NCI-831, NCI-930 (Inc. of Asahi Denka Co., Ltd.), IRGACURE369, IRGACURE907, IRGACUREOXE 01, IRGACURE OXE 02 (Inc. of BASF Co., Ltd.) etc.
In above-mentioned Photoepolymerizationinitiater initiater (C); from the aspect of sensitivity and tone; preferred 2-morpholinyl-2-(4 '-methyl mercapto) benzoyl propane, 9-normal-butyl-3; 6-two (2 '-morpholino isobutyryl) carbazole, more preferably 2-morpholinyl-2-(4 '-methyl mercapto) benzoyl propane.
In coloured composition of the present invention, the content of above-mentioned Photoepolymerizationinitiater initiater (C) is preferably 0.1 ~ 30 quality %, is particularly preferably 0.5 ~ 10 quality % in coloured composition of the present invention.When the content of above-mentioned Photoepolymerizationinitiater initiater (C) is less than 0.1 quality %, the solidification sometimes utilizing exposure to carry out becomes insufficient, and during more than 30 quality %, initiator (C) can be separated out in resin combination sometimes.
Also coloured material (D) can be contained further in coloured composition of the present invention.These coloured materials can be used alone or are mixed with two or more.
As above-mentioned coloured material (D), dyestuff or pigment can be used, such as nitroso compound can be used, nitro-compound, azo-compound, diazonium compound, xanthene compound, quinoline compound, anthraquinone compounds, coumarin compound, phthalocyanine compound, isoindolinone compounds, isoindoline compounds, quinoline Azone compound, anthanthrene dione compounds, purple cyclic ketone compound, perylene compound, Diketopyrrolo-pyrrole compounds, thioindigo compound, dioxazine compound, triphenylmethane compounds, quinophthalone compound, naphthalene tetracarboxylic acid, the metal complex compounds of azoic dyestuff, cyanine dyes, pigment lake, the carbon black obtained by oven process, channel process, hot method or Shawinigan black, Ketjen black or the carbon black such as dim, with epoxy resin above-mentioned carbon black carried out regulate, coating and obtain material, with resin, above-mentioned carbon black is carried out dispersion treatment in a solvent in advance and adsorb 20 ~ 200mg/g resin and obtain material, above-mentioned carbon black carried out acidity or basic surface process and the material, the median size that obtain are more than 8nm and DBP oil number be below 90ml/100g material, by CO, the CO in the volatile component at 950 DEG C 2the whole oxygen amount calculated are every 100m 2surface area blacks is the material of more than 9mg, graphite, graphitized carbon black, gac, carbon fiber, carbon nanotube, coiled carbon fibers (carbonmicrocoil), carbon nanohorn, carbon aerogels, soccerballene, nigrosine, Pigment black 7, titanium are black, in hydrophobic resin, chromoxide green, milori blue, cobalt green, cobalt blue, manganese system, yellow prussiate, phosphoric acid salt ultramarine, Prussian blue, ultramarine, match fine jade peace blue, tie up mineral dye or the pigment dyestuff such as sharp Dean pigment, emerald green, lead sulfate, yellow lead, zinc yellow, red iron oxide (red iron oxide (III)), cadmium red, synthesis iron oxide black, pigment brown.
As above-mentioned coloured material (D), commercially available pigment can also be used, such as, can enumerate Pigment red 1,2,3,9,10,14,17,22,23,31,38,41,48,49,88,90,97,112,119,122,123,144,149,166,168,169,170,171,177,179,180,184,185,192,200,202,209,215,216,217,220,223,224,226,227,228,240,254; Pigment Orange 13,31,34,36,38,43,46,48,49,51,52,55,59,60,61,62,64,65,71; Pigment Yellow 73 1,3,12,13,14,16,17,20,24,55,60,73,81,83,86,93,95,97,98,100,109,110,113,114,117,120,125,126,127,129,137,138,139,147,148,150,151,152,153,154,166,168,175,180,185; Pigment Green 7,10,36; Pigment Blue 15,15:1,15:2,15:3,15:4,15:5,15:6,22,24,56,60,61,62,64; Pigment violet 1,19,23,27,29,30,32,37,40,50 etc.
As above-mentioned coloured material (D), known dyestuff can also be used.As known dyestuff, such as, can enumerate the dyestuffs etc. such as azoic dyestuff, anthraquinone dye, indigoide colors, triarylmethane dye, xanthene dye, alizarine dyestuff, acridine dye, Stilbene dyestuff, thiazole dye, naphthol dye, quinoline dye, nitro-dye, phenylene blue dyestuff, oxazine dye, phthalocyanine pigment, cyanine dyes.
In coloured composition of the present invention, the content of above-mentioned coloured material (D) is preferably 0 ~ 350 mass parts relative to above-mentioned polymerizable compound (B) 100 mass parts with ethylenic unsaturated link(age), is more preferably 0 ~ 250 mass parts.During more than 350 mass parts, employ cured article that coloured composition of the present invention, particularly painted alkali-developable photosensitive composition obtain, the transmittance of display device colour filter reduces, the brightness of display device reduces, therefore not preferred.
Solvent can be added further in coloured composition of the present invention.As this solvent, normally can dissolve or disperse the solvent of above-mentioned each composition (dyestuff (A) etc. be made up of compound of the present invention) as required, such as, can enumerate the ketones such as methylethylketone, methyl amylketone, diethyl ketone, acetone, methyl isopropyl Ketone, methyl iso-butyl ketone (MIBK), pimelinketone, 2-heptanone; The ether series solvents such as ether, diox, tetrahydrofuran (THF), 1,2-glycol dimethyl ether, 1,2-diethoxyethane, dimethyl ether; The ester series solvents such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, hexalin acetate, ethyl lactate, Succinic acid dimethylester, 2,2,4-trimethylammonium-1,3-pentanediol mono isobutyrates (Texanol); The cellosolve such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether series solvent; The alcohol series solvents such as methyl alcohol, ethanol, XOR n-propyl alcohol, XOR propyl carbinol, amylalcohol; The ether-ether series solvents such as ethylene glycol monomethyl acetic ester, ethylene glycol list ethylhexoate, propylene glycol-1-monomethyl ether-2-acetic ester (PGMEA), dipropylene glycol monomethyl ether acetic ester, acetic acid 3-methoxybutyl, ethoxyethyl propionate; The BTX series solvents such as benzene,toluene,xylene; The aliphatic hydrocarbon series solvents such as hexane, heptane, octane, hexanaphthene; The terpenic series hydrocarbon ils such as turps, D-limonene, firpene; The paraffinic hydrocarbons series solvents such as mineral turpentine, Swasol#310 (Cosmo Matsuyama Oil Co., Ltd.), Solvesso#100 (Exxon Chemical Co., Ltd.); The halogenated aliphatic hydrocarbon system solvents such as tetracol phenixin, chloroform, trieline, methylene dichloride, 1,2-ethylene dichloride; The halogenated aromatic hydrocarbon system solvents such as chlorobenzene; Trivalin SF series solvent, aniline, triethylamine, pyridine, acetic acid, acetonitrile, dithiocarbonic anhydride, N, dinethylformamide, N, N-N,N-DIMETHYLACETAMIDE, N-Methyl pyrrolidone, dimethyl sulfoxide (DMSO), water etc., these solvents can use a kind or use as mixed solvent of more than two kinds.In these solvents, ketone, ether-ether series solvent etc., particularly propylene glycol-1-monomethyl ether-2-acetic ester, pimelinketone etc. because of in coloured composition the consistency of resist and Photoepolymerizationinitiater initiater (C) good and preferred.
In coloured composition of the present invention, composition concentration beyond the usage quantity preferred solvent of above-mentioned solvent reaches 5 ~ 30 quality %, when being less than 5 quality %, be difficult to thicken thickness, required wavelength light cannot be absorbed fully, therefore not preferred, and during more than 30 quality %, cause the keeping quality of composition to reduce because of the precipitation of composition or viscosity raising, therefore treatability declines sometimes.
Mineral compound can be contained further in coloured composition of the present invention.As this mineral compound, such as, can enumerate the metal oxides such as nickel oxide, ferric oxide, iridium oxide, titanium oxide, zinc oxide, magnesium oxide, calcium oxide, Lithium Oxide 98min, silicon oxide, aluminum oxide; Layered clay mineral, milori blue, calcium carbonate, magnesiumcarbonate, cobalt system, manganese system, glass powder, mica, talcum, kaolin, yellow prussiate, various metal sulfate, sulfide, selenide, pure aluminium silicate, Calucium Silicate powder, aluminium hydroxide, platinum, gold and silver, copper etc., in these mineral compound, preferential oxidation titanium, silicon oxide, layered clay mineral, silver etc.In coloured composition of the present invention, the content of mineral compound is preferably 0.1 ~ 50 mass parts relative to above-mentioned polymerizable compound (B) 100 mass parts with ethylenic unsaturated link(age), be more preferably 0.5 ~ 20 mass parts, these mineral compound can use one kind or two or more.
These mineral compound such as can be used as weighting agent, antireflection agent, conductive agent, stablizer, fire retardant, physical strength rising agent, special wavelength absorption agent, the agent of oleophobic ink etc.
In coloured composition of the present invention, when using pigment and/or mineral compound, dispersion agent can be added.As this dispersion agent, as long as pigment, mineral compound can be made to disperse and stable dispersion agent, any dispersion agent can be used, commercially available dispersion agent, such as BYK Chemie Inc. BYK series etc. can be used, preferably use be made up of the polyester with basic functionality, polyethers, urethane macromolecule dispersing agent, have nitrogen-atoms as basic functionality and the functional group with nitrogen-atoms be amine and/or its quaternary salt, amine value is the dispersion agent of 1 ~ 100mgKOH/g.
In addition, in coloured composition of the present invention, can add as required thermal polymerization inhibitors such as methyl-phenoxide, Resorcinol, pyrocatechol, tert-butyl catechol, thiodiphenylamine; Softening agent; Adhesion promoters; Weighting agent; Defoamer; Flow agent; Surface conditioner; Antioxidant; UV light absorber; Dispersing auxiliary; Anti-agglutinant; Catalyzer; Effect promotor; Linking agent; The additive that tackifier etc. are conventional.
In coloured composition of the present invention, above-mentioned dyestuff (A), above-mentioned there is ethylenic unsaturated link(age) polymerizable compound (B) and Photoepolymerizationinitiater initiater (C) beyond the content of any composition (but coloured material (D) and solvent except) suitably select according to its application target, be not particularly limited, but preferably add up to below 50 mass parts relative to above-mentioned content 100 mass parts with the polymerizable compound (B) of ethylenic unsaturated link(age).
In coloured composition of the present invention, also by using other organic polymer together with the above-mentioned polymerizable compound (B) with ethylenic unsaturated link(age), thus improve the characteristic of the cured article be made up of coloured composition of the present invention.As above-mentioned organic polymer, such as polystyrene can be enumerated, polymethylmethacrylate, Eudragit NE30D, poly-(methyl) vinylformic acid, vinylbenzene-(methyl) acrylic copolymer, (methyl) acryl acid-methyl methacrylate copolymer, ethylene-vinyl chloride copolymer, ethylene-vinyl base co-polymer, polyvinyl chloride (PVC) RESINS, ABS resin, nylon 6, nylon66 fiber, nylon 12, urethane resin, polycarbonate polyvinyl butyral acetal, cellulose ester, polyacrylamide, saturated polyester, resol, phenoxy resin, polyamide-imide resin, polyamic acid resin, epoxy resin etc., wherein, preferred polystyrene, (methyl) acryl acid-methyl methacrylate copolymer, epoxy resin.
When using other organic polymer, its usage quantity is preferably 10 ~ 500 mass parts relative to above-mentioned polymerizable compound (B) 100 mass parts with ethylenic unsaturated link(age).
Can also further also with chain-transfer agent, sensitizing agent, tensio-active agent, silane coupling agent, melamine compound etc. in coloured composition of the present invention.
As above-mentioned chain-transfer agent or sensitizing agent, usually use the compound containing sulphur atom.Such as Thiovanic acid can be enumerated, mercaptosuccinic acid, thiosalicylic acid, 2 mercaptopropionic acid, 3-thiohydracrylic acid, 3-mercaptobutyric acid, N-(2-mercapto radical propionyl group) glycine, 2-mercaptonicotinic acid, 3-[N-(2-mercaptoethyl) carbamyl] propionic acid, 3-[N-(2-mercaptoethyl) is amino] propionic acid, N-(3-mercapto radical propionyl group) L-Ala, mistabrom, 3-thiohydracrylic acid, 4-sulfydryl fourth sulfonic acid, dodecyl (4-methylthio group) phenyl ether, 2 mercapto ethanol, 3-Mercapto-1，2-propanediol, 1-sulfydryl-2-propyl alcohol, 3-sulfydryl-2-butanols, mercapto-phenol, 2-MEA, 2-mercaptoimidazole, 2-mercaptobenzimidazole, 2-sulfydryl-3-pyridone, 2-mercaptobenzothiazole, Thiovanic acid, trimethylolpropane tris (3-mercaptopropionic acid ester), the sulfhydryl compounds such as tetramethylolmethane four (3-mercaptopropionic acid ester), the di-sulphide compounds that the oxidation of this sulfhydryl compound is obtained, iodoacetic acid, iodopropionic acid, ethylene iodohydrin, 2-iodine ethyl sulfonic acid, the iodate alkylates such as 3-iodine propanesulfonic acid, trimethylolpropane tris (3-mercaptoisobutanoic acid esters), butyleneglycol two (3-mercaptoisobutanoic acid esters), ethanthiol, the last of the ten Heavenly stems two mercaptan, Isosorbide-5-Nitrae-dimethyl sulfydryl benzene, the two thiopropionate of butyleneglycol, the two mercaptoacetate of butyleneglycol, ethylene glycol bis mercaptoacetate, trimethylolpropane tris mercaptoacetate, the two thiopropionate of butyleneglycol, trimethylolpropane tris thiopropionate, trimethylolpropane tris mercaptoacetate, tetramethylolmethane tetrathio propionic ester, tetramethylolmethane four mercaptoacetate, trihydroxy-ethyl trithio propionic ester, compound shown in following compound N o.C1, the aliphatics multi-functional thiol compounds such as tri-thiol propionic acid three (2-hydroxyethyl) isocyanuric acid ester, Showa electrician Inc. KARENZ MTBD1, PE1, NR1 etc.
As above-mentioned tensio-active agent, can use the tensio-active agents such as the nonionogenic tensides such as positively charged ion system tensio-active agent, polyethylene glycol alkyl ether, cithrol, sorbitan-fatty acid ester, glycerine monofatty ester, amphoterics, silicone-based tensio-active agent such as negatively charged ion system tensio-active agent, higher amines halogen acid salt, quaternary ammonium salt such as the fluorine surfactant such as perfluoralkyl phosphate, perfluoroalkyl carboxylate, higher aliphatic acid-alkali salt, alkylsulfonate, alkyl-sulphate, they also can combinationally use.
As above-mentioned silane coupling agent, such as, can use chemical company of SHIN-ETSU HANTOTAI silane coupling agent, wherein preferably use KBE-9007, KBM-502, KBE-403 etc. to have the silane coupling agent of isocyanate group, methacryloyl or epoxy group(ing).
As above-mentioned melamine compound, the active methylol (CH in the nitrogen compounds such as (gathering) melamine methylol, (gathering) methylol glycoluril, (gathering) methylolbenzoguanamine, (gathering) methylolurea can be enumerated 2oH yl) all or part of (at least 2) by alkyl etherified compound.At this, as the alkyl forming alkyl oxide, methyl, ethyl or butyl can be enumerated, can be mutually the same, also can be different.In addition, about not by alkyl etherified methylol, can in a part self-condensation, also can form oligopolymer composition at two intermolecular condensations.Specifically, HMMM, six butoxymethyl trimeric cyanamides, tetramethoxymethylglycoluril, four butoxymethyl glycolurils etc. can be used.Wherein, preferred HMMM, six butoxymethyl trimeric cyanamides etc. are by alkyl etherified trimeric cyanamide.
Coloured composition of the present invention can adopt spin coater, roller coating machine, bar coater, mould painting machine, curtain coater, various printing, the known means of impregnating to be applied in the support substrate such as soda-lime glass, silica glass, semiconductor substrate, metal, paper, plastics.In addition, also can first be transferred in other support substrate after application in the support substrate such as film, its application method limit.
In addition, as the light source of the active light used when making coloured composition of the present invention solidify, can use and send the light source that wavelength is the light of 300 ~ 450nm, such as, can use ultrahigh pressure mercury lamp, mercury vapour arc lamp, carbon arc lamp, xenon arc lamp etc.
In addition, the direct picture of laser not using mask can directly form image by the numerical information of computer etc. by using laser in exposure light source can also improve resolving power or positional precision etc. owing to boosting productivity, therefore be useful, as this laser, the light of the wavelength of preferred use 340 ~ 430nm, also can use Argon ion laser, helium-neon laser, YAG laser and semiconductor laser etc. to send laser apparatus from the light can seeing region of ultra-red.When using these laser apparatus, the sensitizing coloring matter absorbed from the light can seeing infrared region can be added.
Coloured composition of the present invention (or its cured article) can be used for following various uses: light solidity coating or varnish, light solidity caking agent, printed base plate or color TV, PC watch-dog, portable information terminal, colour filter in the display panels of the colour such as digital camera display, the colour filter of ccd image sensor, the electrode materials of plasma display, powder coating, printing-ink, press plate, caking agent, gear division composition, light chisel resin, jelly paint, the photo-resist of electronic engineering, platedresist, etching resist, aqueous and desciccator diaphragm, solder resist, for the manufacture of the resist of the colour filter of various display purposes or at plasma display, the resist of structure is formed in the manufacturing process of el display device and LCD, for enclosing the composition of Electrical and Electronic part, solder resist, magnetic recording material, milli machine part, waveguide, photoswitch, plating mask, etching mask, color test system, glass fiber cable coatings, silk screen printing masterplate, for being manufactured the material of three-dimensional body by stereolithography, holographic recording material, image recording material, fine electronic circuit, decoloring material, for the decoloring material of image recording material, use the decoloring material of the image recording material of microcapsule, use in printed circuit board photo anti-corrosion agent material, the photo anti-corrosion agent material of UV and visible laser through image system, for tellite successively stacked in the photo anti-corrosion agent material that formed of dielectric layer or protective membrane etc., its purposes is not particularly limited.
Coloured composition of the present invention is when for painted alkali-developable photosensitive composition, use for the purpose of the pixel forming colour filter, the photosensitive composite particularly as the display device colour filter for the formation of the device used for image display such as display panels, organic EL is useful.
In addition, display device colour filter of the present invention, except cured article of the present invention, also can have red, green, blue, orange, purple and black optical parameter.
Aforementioned display device part colour filter is formed preferably by following operation: (1) forms the operation of the film of coloured composition of the present invention (particularly painted alkali-developable photosensitive composition) on substrate; (2) via the mask of pattern form with regulation, this film is irradiated to the operation of active light; (3) developing solution (particularly alkaline developer) is utilized the tunicle after exposure to be carried out the operation of developing; (4) this tunicle after development is carried out the operation heated.In addition, coloured composition of the present invention is also useful as not having the coloured composition of the ink-jetting style of developing procedure, transfer modes.
Manufacture for the colour filter of display panels etc. can use the present invention or other coloured composition, repeatedly carry out the operation of above-mentioned (1) ~ (4) is undertaken combining making by patterns more than 2 looks.
Embodiment
Below enumerate embodiment and comparative example illustrates the present invention in more detail, but the present invention is not defined in these embodiments.
Embodiment 1-1 ~ 1-8 represents the preparation example of the painted alkali-developable photosensitive composition No.1 ~ No.8 as coloring photosensitive combination of the present invention, and comparative example 1-1 and 1-2 represents the preparation example of more painted alkali-developable photosensitive composition No.1 and No.2.
In evaluation Example 1-1 ~ 1-8, the thermotolerance of the painted alkali-developable photosensitive composition No.1 ~ No.8 obtained in embodiment 1-1 ~ 1-8 is evaluated, in comparative evaluation example 1-1 and 1-2, the thermotolerance of more painted alkali-developable photosensitive composition No.1 and No.2 obtained in comparative example 1-1 and 1-2 is evaluated.
The preparation of [embodiment 1-1 ~ 1-8 and comparative example 1-1 and 1-2] painted alkali-developable photosensitive composition No.1 ~ No.8 and more painted alkali-developable photosensitive composition No.1 and No.2
The preparation of < step 1 > alkali-developable photosensitive composition
Mix as ACA Z251 (Daicel-Cytec Inc.) 30.33g and AronixM-450 (East Asia Synesis Company system) 11.04g, IRGACURE907 (BASF AG's system) 1.93g as (C) composition of (B) composition, the PGMEA 36.60g as (E) composition and pimelinketone 20.08g and FZ2122 (the Dow Corning Toray Inc.) 0.01g as other compositions, carry out stirring until insolubles disappears, obtain alkali-developable photosensitive composition.
< step 2 > dye solution No.1 ~ No.8 and compare the preparation of dye solution No.1 and No.2
Add as (A) composition compound N o.2 ~ 0.10g of pair (trifluoromethane sulfonyl group) imide salts of No.4, No.17, No.18 and No.20 ~ No.22 and comparative compound No.1 and No.2 and N,N-DIMETHYLACETAMIDE 1.90g; carrying out stirring makes it dissolve, and makes dye solution No.1 ~ No.8 and compares dye solution No.1 and No.2.
The preparation of < step 3 > painted alkali-developable photosensitive composition No.1 ~ No.8 and more painted alkali-developable photosensitive composition No.1 and No.2
The 1.0g of each dye solution of the corresponding No. obtained in the 5.0g of each alkali-developable photosensitive composition obtained in step 1 and step 2 is mixed respectively, carry out stirring until become even, obtain painted alkali-developable photosensitive composition No.1 ~ No.8 and more painted alkali-developable photosensitive composition No.1 and No.2.
[evaluation Example 1-1 ~ 1-8 and comparative evaluation example 1-1 ~ 1-2] utilizes and burns till the Evaluation of Heat Tolerance carried out
Under the condition of 410rpm × 7 second, more painted alkali-developable photosensitive composition No.1 and No.2 obtained in the painted alkali-developable photosensitive composition No.1 ~ No.8 obtained in embodiment 1-1 ~ 1-8 and comparative example 1-1 and 1-2 is coated with on the glass substrate, utilizes hot-plate to be dried (90 DEG C, 90 seconds).Ultrahigh pressure mercury lamp is utilized to expose (150mJ/cm to gained film 2).Under the condition of 230 DEG C × 30min, the film after exposure is burnt till.Measure the film absorbancy of (exposure after) and the film absorbancy after burning till before burning till under the maximum absorption wavelength (λ max) of compound used therefor (dyestuff), evaluate as with the relative intensity when film absorbancy of (after exposure) is 100 before burning till.In addition, close to 100, the absorbancy of the film after burning till more represents that thermotolerance is higher.Also inquire into aberration (the Δ E before and after burning till in addition ab*).Show the result in [table 1].
[table 1]
Compound (dyestuff) Aberration Δ Eab*
Evaluation Example 1-1 Compound N o.2 3.48
Evaluation Example 1-2 Compound N o.3 3.94
Evaluation Example 1-3 Compound N o.4 2.07
Evaluation Example 1-4 Compound N o.17 2.70
Evaluation Example 1-5 Compound N o.18 2.22
Evaluation Example 1-6 Compound N o.20 3.97
Evaluation Example 1-7 Compound N o.21 4.70
Evaluation Example 1-8 Compound N o.22 4.02
Comparative evaluation example 1-1 Comparative compound No.1 16.6
Comparative evaluation example 1-2 Comparative compound No.2 5.38
[evaluation Example 2-1 ~ 2-8 and comparative evaluation example 2-1 ~ 2-2] solvability evaluation
Each 0.1g of compound N o.2 ~ 4, No.17, No.18 and No.20 ~ No.22, comparative compound No.1 and No.2 is stirred and drips propylene glycol-1-monomethyl ether-2-acetic ester, concentration when dissolving completely is evaluated as solubleness.
[table 2]
Compound (dyestuff) Solvability
Evaluation Example 2-1 Compound N o.2 10＜
Evaluation Example 2-2 Compound N o.3 10＜
Evaluation Example 2-3 Compound N o.4 10＜
Evaluation Example 2-4 Compound N o.17 10＜
Evaluation Example 2-5 Compound N o.18 10＜
Evaluation Example 2-6 Compound N o.20 10＜
Evaluation Example 2-7 Compound N o.21 10＜
Evaluation Example 2-8 Compound N o.22 10＜
Comparative evaluation example 2-1 Comparative compound No.1 4
Comparative evaluation example 2-2 Comparative compound No.2 2
From the above results, compound of the present invention is used as the painted alkali-developable photosensitive composition of dyestuff because the compound used as dyestuff is at the R corresponding to formula (I) 1, R 2and R 3position on there is at least two places substituting group beyond hydrogen, therefore aberration is with low uncertainty, and thermotolerance is high.
On the other hand, employ the painted alkali-developable photosensitive composition of comparative compound No.1 as dyestuff and correspond to the R in formula (I) due to the compound that uses as dyestuff 1, R 2and R 3position on only at a place, there is the substituting group beyond hydrogen, therefore poor heat resistance.
In addition, although employ the compound that the painted alkali-developable photosensitive composition of comparative compound No.2 as dyestuff use as dyestuff to correspond to the R in formula (I) 1, R 2and R 3position at Liang Chu, there is substituting group beyond hydrogen, but solvability or poor.
Therefore, be useful as employing the coloring photosensitive combination of the present invention of compound of the present invention as the painted alkali-developable photosensitive composition of dyestuff for display device colour filter.

Claims (5)

1. a coloring photosensitive combination, it contains the dyestuff (A) be made up of the compound shown in following general formula (I), the polymerizable compound (B) with ethylenic unsaturated link(age) and Photoepolymerizationinitiater initiater (C),
In formula, R 1, R 2, R 3, R 20, R 21, R 22, R 23, R 24, R 25, R 26, R 27and R 28represent hydrogen atom or halogen atom independently of one another, be the alkyl of 1 ~ 8 by cyano group, nitro, hydroxyl, the substituted or unsubstituted carbonatoms of halogen atom, by the substituted or unsubstituted carbonatoms of halogen atom be 6 ~ 12 aryl, be the arylalkyl of 7 ~ 20 or the substituting group that represents with-X-Y by the substituted or unsubstituted carbonatoms of halogen atom; X represents Sauerstoffatom or sulphur atom; Y represent by the substituted or unsubstituted carbonatoms of halogen atom be 1 ~ 8 alkyl, be the aryl of 6 ~ 12 by the substituted or unsubstituted carbonatoms of halogen atom or be the arylalkyl of 7 ~ 20 by the substituted or unsubstituted carbonatoms of halogen atom;
R 4, R 5, R 6, R 7, R 8and R 9represent hydroxyl or halogen atom independently of one another, be the alkyl of 1 ~ 8 by the substituted or unsubstituted carbonatoms of cyano group, nitro, hydroxyl or halogen atom, by carbonatoms be 1 ~ 4 alkyl, halogen atom, cyano group or vinyl substituted or unsubstituted phenyl, by carbonatoms be 1 ~ 4 alkyl, halogen atom, cyano group or vinyl substituted or unsubstituted benzyl; R 4with R 5, R 6with R 7, and R 8with R 9also can be connected to form the heterocycle of 3 ~ 6 rings;
R 1, R 2and R 3in at least 2 be substituting group beyond hydrogen atom;
An q-represent the negatively charged ion of q valency, q represent 1 or 2, p represent electric charge remained neutral coefficient.
2. coloring photosensitive combination according to claim 1, is characterized in that, the R in described general formula (I) 1, R 2and R 3in any more than 2 be halogen atom, be the alkyl of 1 ~ 8 by the substituted or unsubstituted carbonatoms of halogen atom.
3. coloring photosensitive combination according to claim 1 and 2, it is also further containing more than one coloured material (D), but except the dyestuff be made up of the compound shown in described general formula (I) in this coloured material (D).
4. a cured article, the cured article of its coloring photosensitive combination according to any one of claims 1 to 3.
5. a display device colour filter, it is possessing cured article according to claim 4 at least partially.
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